Untangling Email (and a few other things)

This started as a simple cleanup.

It didn’t stay that way.

I wanted to move my personal email to Fastmail, consolidate a few domains, and finally stop carrying around a decade of accidental decisions. In theory, this should have taken an afternoon.

Instead, it turned into a single, very long evening — about five hours of focused work, context-switching, and realizing just how much invisible complexity I’d accumulated over time.

The mess I was carrying

At the start of this, I had:

• Three personal domains
• Office 365 (historical, mostly inertia)
• Gmail (mostly spam and signups)
• iCloud mail (a long-running mistake)
• Contacts scattered across providers
• Calendars syncing to places I couldn’t even identify anymore

None of this was broken.
It was just… unintentional.

Every system had a reason for existing at the time.
None of them had been questioned recently.

That’s how technical debt actually forms.

Moving the mail

I migrated roughly five years of email into Fastmail.

That part was surprisingly painless:

• IMAP imports worked
• Folder structure came across cleanly
• Sent mail, archives, and weird edge folders all landed where I expected

The real work started after the import finished.

That’s when you realize email isn’t just mail.
It’s receipts.
Conversations.
Proof of life.
Things you can’t quite delete yet.

I didn’t do a “clean inbox” fantasy reset.

I did something quieter:

• kept what still had meaning
• archived what was done
• deleted what I didn’t need to keep carrying

No mass purge.
Just decisions.

Contacts: the real nightmare

Email was easy.
Contacts were not.

Over the years, I’d accumulated duplicates across:

• Outlook
• Gmail
• iCloud
• random CardDAV syncs I forgot I ever enabled

Same people.
Different formats.
Different numbers.
Different versions of who they once were.

Some contacts were active relationships.
Some were long-dormant.
Some were people I hadn’t spoken to in a decade but still couldn’t quite delete.

And then there were the harder ones.

Names of people who are gone.
Parents.
Friends.
Voices that don’t answer anymore.

Deleting them felt less like cleanup and more like erasure — like pretending they never existed at all.

I merged.
Deduplicated.
Grouped.
Deleted what I could.
Left what I wasn’t ready to let go of.

Then did it again.

When I finally looked up, I had fewer contacts — and not because everything was resolved, but because I’d been honest about what still belonged with me.

I didn’t finish the job.

But I stopped carrying quite so much weight in my pocket.

The iPhone reckoning

This is where things got uncomfortable.

Modern iOS makes it very easy to add accounts.
It does not make it easy to understand what is actually syncing where.

Mail.
Contacts.
Calendars.
Passwords.
Keychains.

All “on,” all the time — until they aren’t, and you no longer remember why.

Over the years, my phone had quietly become a convergence point for identities I was trying to keep separate: personal, professional, legacy, and accidental. Apple, Microsoft, and Google were all present, all syncing something, all assuming they were the center of the universe.

I didn’t want that anymore.

My goal wasn’t to abandon the iPhone or pretend I could escape ecosystems entirely. It was to reduce my dependence on any single one — and to be able to move my identity if I ever needed to.

So I stripped it back.

I removed everything:

• Exchange
• Gmail
• iCloud mail
• personal accounts I no longer trusted or understood

Then I added things back intentionally, as distinct lanes:

• Outlook — work only
• Gmail — spam, signups, throwaway identity
• Fastmail — my personal identity

Fastmail came back first, using app-specific credentials, not a shared cloud assumption.

Mail.
Contacts.
Calendars.

Nothing else.

iCloud stayed, but nerfed as much as Apple allows — no mail, no contacts, no calendars, no quiet authority over my data.

When I finished, something subtle but important changed.

My phone felt predictable again.

Not because it was simpler, but because each system had a clear role — and none of them got to blur into the others without my consent.

DNS, certificates, and knowing when to stop

At some point, I went too far.

I tried to make mail.<domain> or inbox.<domain> behave exactly the way I wanted in the browser. That’s when certificates, DNS authority, and reality stepped in to remind me:

Not everything needs to be perfect.
Some things just need to work.

Fastmail works.
The default URLs work.
The email works.

I don’t need to win an argument with TLS at midnight.

That part can wait.

What this was actually about

This wasn’t really about email.

It was about boundaries.

Between:

• personal and professional
• intentional and inherited
• things I still use and things I keep “just in case”

Email is deceptively intimate.
It quietly accumulates years of context.
Moving it forces you to decide what version of yourself you’re still carrying forward.

I didn’t want a zero-inbox productivity fantasy.
I wanted something quieter:

• one system
• one mental model
• fewer surprises

That’s what I ended up with.

Where I landed

Today, I have:

• One primary personal email system
• Three domains, intentionally routed
• A phone that syncs only what I trust
• Contacts that mostly reflect my real life
• Calendars that don’t argue with each other

It’s not minimal.
It’s deliberate.

And that’s enough.

The pattern (again)

I keep relearning the same lesson:

Most technical cleanups aren’t blocked by tools.
They’re blocked by hesitation.

Once you stop optimizing and start deciding, things move quickly.

Email included.